I am wondering if you have any advice on trying to move a friendship into something more romantic.
This wonderful girl came to work for my company and ever since she walked in the door I have thought she was absolutely amazing. We share many similarities in our interests, sense of humor, and professional aspirations. In the year that we have worked together we have become friends, spending time with other groups of colleagues as well as with each other’s friends in groups, but we have kept our one-on-one alone time very limited.
I never pursued a romantic relationship with her since we work together, and she reports to me in a number of instances. But now? The situation is changing. We’re both leaving our current company and moving on to separate jobs.
I would love to move things in a more romantic direction, but I have the age old dilemma of risking the friendship. How do I approach this situation with the possibility of preserving a friendship should I get rejected?
Good call on keeping things strictly friendly with this lady thus far. It is all kinds of complicated (and often forbidden) to get involved with a subordinate. Waiting it out was the right thing to do.
Here’s the short of it. Anytime you try to move a relationship from friendship to romance, you risk ruining the friendship. There isn’t any magical way to find out if she like likes you or put the moves on her or try out a relationship without risking an awkward, embarrassing situation that could blow up in your face. It’s an all or nothing situation, you know? I mean, this scenario doesn’t really work:
You: I was wondering if you’d like to go on a date with me.
Her: Oh…um…I’m sorry, I don’t feel that way about you.
You: No, me neither, just kidding.
“Right in front of our eyes…We’ve been so blind, but baby now we see–“
Once you ask her out or lean in for the kiss, that’s it, you can’t walk it back. In the event that you do tell her how you feel and it’s unrequited, your friendship won’t remain untouched. If you tell her you want to date her and she isn’t interested, you’ll feel awkward or she’ll feel awkward, or most likely, you’ll both feel awkward. It’s sort of like a power shift. She’ll know you’re pining for her and that will make her feel weird…you’ll be pining for her and that will make you feel weird.
So you have to risk the friendship in order to find out if she has the same feelings as you do. You have a choice–throw caution (and the friendship) to the wind and ask her out, or leave it be and remain friends indefinitely. I’ve been where you are and I have to say…unless you are extraordinarily adjusted, reasonable, and divorced from your emotions, it’s probably going to be difficult for you to just remain friends with this woman. A friendship may have been okay in the past because you had your professional responsibilities preventing you from taking it any further. But now there’s no barrier and because you want a deeper level of intimacy, your relationship as friends is going to be pretty unsatisfying. You’ll always be thinking about how you want more from her.
Want this happy ending? You’ll have to take a risk.
Of course, it’s your call, and you should only do what you feel comfortable with, but…I say go for it. Ask her out, sweep her off her feet, try to take it to the next level. I’m always a proponent of taking chances when it comes to love. Dive in with both feet and don’t look back. I’ll be rooting for you from afar.
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